TWI481594B - 可再生資源中異戊二烯之純化 - Google Patents
可再生資源中異戊二烯之純化 Download PDFInfo
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- TWI481594B TWI481594B TW099144617A TW99144617A TWI481594B TW I481594 B TWI481594 B TW I481594B TW 099144617 A TW099144617 A TW 099144617A TW 99144617 A TW99144617 A TW 99144617A TW I481594 B TWI481594 B TW I481594B
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- Prior art keywords
- isoprene
- solvent
- methyl
- column
- gas
- Prior art date
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- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 988
- 238000000746 purification Methods 0.000 title description 26
- 239000002904 solvent Substances 0.000 claims description 195
- 239000007789 gas Substances 0.000 claims description 188
- 238000000034 method Methods 0.000 claims description 178
- 239000012535 impurity Substances 0.000 claims description 175
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- 239000006227 byproduct Substances 0.000 claims description 114
- 238000001179 sorption measurement Methods 0.000 claims description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 47
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 24
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- 238000009835 boiling Methods 0.000 claims description 19
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- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
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- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- CBIDRCWHNCKSTO-UHFFFAOYSA-N prenyl diphosphate Chemical compound CC(C)=CCO[P@](O)(=O)OP(O)(O)=O CBIDRCWHNCKSTO-UHFFFAOYSA-N 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001184 proton transfer reaction mass spectrometry Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/173—Alkadienes with five carbon atoms
- C07C11/18—Isoprene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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| EP2310490B1 (en) | 2008-07-02 | 2019-01-02 | Danisco US Inc. | Methods for producing isoprene |
| US8324442B2 (en) | 2009-03-03 | 2012-12-04 | Amyris, Inc. | Microbial derived isoprene and methods for making the same |
| TW201412988A (zh) * | 2009-06-17 | 2014-04-01 | Danisco Us Inc | 使用ｄｘｐ及ｍｖａ途徑之改良之異戊二烯製造 |
| TWI434921B (zh) * | 2009-06-17 | 2014-04-21 | Danisco Us Inc | 從生物異戊二烯組合物製造燃料成分之方法及系統 |
| JP5643838B2 (ja) * | 2009-12-18 | 2014-12-17 | ダニスコ・ユーエス・インク | 再生可能資源からのイソプレンの精製 |
| CN102906269A (zh) * | 2009-12-22 | 2013-01-30 | 丹尼斯科美国公司 | 用于增加异戊二烯气体产量的膜生物反应器 |
| EP2582649A1 (en) | 2010-06-17 | 2013-04-24 | Danisco US Inc. | Fuel compositions comprising isoprene derivatives |
| EP2601300A1 (en) | 2010-08-06 | 2013-06-12 | Danisco US Inc. | Production of isoprene under neutral ph conditions |
| CN103443271A (zh) | 2010-10-27 | 2013-12-11 | 丹尼斯科美国公司 | 用于增加异戊二烯产量的异戊二烯合酶变体 |
| BR112013016264A2 (pt) | 2010-12-22 | 2018-06-19 | Danisco Us Inc | produção biológica de açúcares de pentose com o uso de células recombinantes |
| WO2012088462A1 (en) | 2010-12-22 | 2012-06-28 | Danisco Us Inc. | Compositions and methods for improved isoprene production using two types of ispg enzymes |
| AU2012249389A1 (en) | 2011-04-29 | 2013-11-14 | Danisco Us Inc. | Production of mevalonate, isoprene, and isoprenoids using genes encoding polypeptides having thiolase, HMG-CoA synthase and HMG-CoA reductase enzymatic activities |
| BR112013027555A2 (pt) | 2011-04-29 | 2021-08-10 | Danisco Us Inc. | células recombinantes capazes de maior produção de isopreno, mevalonato e isoprenoides e método para produzir isopreno, mevalonato e isoprenoides |
| WO2013022799A1 (en) | 2011-08-05 | 2013-02-14 | Danisco Us Inc. | PRODUCTION OF ISOPRENOIDS UNDER NEUTRAL pH CONDITIONS |
| EP2764084B2 (en) | 2011-10-07 | 2021-11-03 | Danisco US Inc. | Utilization of phosphoketolase in the production of mevalonate, isoprenoid precursors, and isoprene |
| US8735134B2 (en) | 2011-10-27 | 2014-05-27 | Danisco Us Inc. | Isoprene synthase variants with improved solubility for production of isoprene |
| BR112014014947A2 (pt) | 2011-12-23 | 2020-10-27 | Danisco Us Inc. | produção acentuada de isopreno com o uso de células hospedeiras tendo atividade de ispa diminuida |
| US9315831B2 (en) | 2012-03-30 | 2016-04-19 | Danisco Us Inc. | Direct starch to fermentable sugar as feedstock for the production of isoprene, isoprenoid precursor molecules, and/or isoprenoids |
| WO2013155053A1 (en) * | 2012-04-09 | 2013-10-17 | Michigan Biotechnology Institute | Process for reducing methyl butenol (2-methyl-3-buten-2-ol) |
| US9163263B2 (en) | 2012-05-02 | 2015-10-20 | The Goodyear Tire & Rubber Company | Identification of isoprene synthase variants with improved properties for the production of isoprene |
| US8895277B2 (en) | 2012-05-02 | 2014-11-25 | Danisco Us Inc. | Legume isoprene synthase for production of isoprene |
| JP6010343B2 (ja) * | 2012-05-21 | 2016-10-19 | 株式会社ブリヂストン | イソプレン−ブタジエン共重合体、イソプレン−ブタジエン共重合体の製造方法、ゴム組成物及びタイヤ |
| JP6010342B2 (ja) * | 2012-05-21 | 2016-10-19 | 株式会社ブリヂストン | イソプレン−ブタジエン共重合体、イソプレン−ブタジエン共重合体の製造方法、ゴム組成物及びタイヤ |
| JP6074161B2 (ja) * | 2012-05-22 | 2017-02-01 | 株式会社ブリヂストン | ゴム組成物およびタイヤの製造方法 |
| JP6074160B2 (ja) * | 2012-05-22 | 2017-02-01 | 株式会社ブリヂストン | ゴム組成物およびタイヤの製造方法 |
| WO2013181647A2 (en) | 2012-06-01 | 2013-12-05 | Danisco Us Inc. | Compositions and methods of producing isoprene and/or industrrial bio-products using anaerobic microorganisms |
| JP2016511630A (ja) | 2012-12-21 | 2016-04-21 | ダニスコ・ユーエス・インク | 代案の下流メバロン酸経路を使用するイソプレン、イソプレノイド、およびイソプレノイド前駆体の生成 |
| WO2014121357A1 (en) * | 2013-02-07 | 2014-08-14 | Braskem S.A. | Method of separating and purifying a conjugated diolefin produced by fermentation under anaerobic conditions |
| US9850512B2 (en) | 2013-03-15 | 2017-12-26 | The Research Foundation For The State University Of New York | Hydrolysis of cellulosic fines in primary clarified sludge of paper mills and the addition of a surfactant to increase the yield |
| EP2980221B1 (en) | 2013-03-29 | 2019-08-21 | Ajinomoto Co., Inc. | Method for collecting isoprene contained in fermented gas, and method for producing purified isoprene |
| BR112015025489A2 (pt) | 2013-04-10 | 2017-10-10 | Danisco Us Inc | fosfocetolases para produção melhorada de metabolitos derivados de acetil coenzima a, isopreno, precursores de isoprenoides, e isoprenoides |
| CN105518130A (zh) | 2013-06-21 | 2016-04-20 | 丹尼斯科美国公司 | 用于梭菌转化的组合物和方法 |
| WO2015081406A1 (en) * | 2013-12-02 | 2015-06-11 | Braskem S.A. | Fermentation hydrocarbon gas products separation via membrane |
| WO2015127305A2 (en) | 2014-02-20 | 2015-08-27 | Danisco Us Inc. | Recombinant microorganisms for the enhanced production of mevalonate, isoprene, isoprenoid precursors, isoprenoids, and acetyl-coa-derived products |
| WO2015127435A1 (en) * | 2014-02-24 | 2015-08-27 | Glycos Biotechnologies, Inc. | Recovery of isoprene from fermentation processes using mechanical compression and condensation |
| US9951363B2 (en) | 2014-03-14 | 2018-04-24 | The Research Foundation for the State University of New York College of Environmental Science and Forestry | Enzymatic hydrolysis of old corrugated cardboard (OCC) fines from recycled linerboard mill waste rejects |
| CN106866341B (zh) * | 2017-01-20 | 2019-08-06 | 中国科学院青岛生物能源与过程研究所 | 一种分离回收发酵尾气中低浓度异戊二烯的方法 |
| FI128295B (en) * | 2017-12-29 | 2020-02-28 | Neste Oyj | Renewable, highly isoparaffinic solvent-based distillate |
| CN110354644A (zh) * | 2018-04-10 | 2019-10-22 | 天津科技大学 | 一种高效的醋酸丁酯废气吸收与解吸装置 |
| CN111454114B (zh) * | 2020-05-11 | 2023-07-14 | 长沙贝塔医药科技有限公司 | 一种用13c2-香叶醇合成高纯度13c2-月桂烯的方法 |
| US12350968B2 (en) | 2022-09-19 | 2025-07-08 | The Goodyear Tire & Rubber Company | Sustainable tire |
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-
2010
- 2010-12-15 JP JP2012544763A patent/JP5643838B2/ja not_active Expired - Fee Related
- 2010-12-15 CN CN201080064167.4A patent/CN102884028B/zh not_active Expired - Fee Related
- 2010-12-15 EP EP10799184A patent/EP2513021A2/en not_active Withdrawn
- 2010-12-15 WO PCT/US2010/060552 patent/WO2011075534A2/en active Application Filing
- 2010-12-15 CA CA2783976A patent/CA2783976A1/en not_active Abandoned
- 2010-12-15 US US12/969,440 patent/US8569562B2/en active Active
- 2010-12-15 AU AU2010331946A patent/AU2010331946A1/en not_active Abandoned
- 2010-12-15 SG SG2012042511A patent/SG181605A1/en unknown
- 2010-12-15 IN IN5187DEN2012 patent/IN2012DN05187A/en unknown
- 2010-12-15 BR BR112012014736A patent/BR112012014736B1/pt not_active IP Right Cessation
- 2010-12-17 TW TW099144617A patent/TWI481594B/zh active
- 2010-12-20 AR ARP100104783A patent/AR079560A1/es unknown
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2013
- 2013-09-24 US US14/035,746 patent/US20140187839A1/en not_active Abandoned
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2014
- 2014-09-10 JP JP2014184058A patent/JP6378013B2/ja not_active Expired - Fee Related
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2015
- 2015-04-09 US US14/682,930 patent/US9751820B2/en active Active
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2016
- 2016-11-18 JP JP2016225310A patent/JP2017081924A/ja active Pending
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| AR079560A1 (es) | 2012-02-01 |
| US9751820B2 (en) | 2017-09-05 |
| AU2010331946A2 (en) | 2012-07-19 |
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| JP2015007119A (ja) | 2015-01-15 |
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| CN102884028B (zh) | 2015-08-19 |
| AU2010331946A1 (en) | 2012-06-28 |
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| SG181605A1 (en) | 2012-07-30 |
| BR112012014736A2 (pt) | 2016-04-19 |
| TW201139367A (en) | 2011-11-16 |
| JP2017081924A (ja) | 2017-05-18 |
| EP2513021A2 (en) | 2012-10-24 |
| CA2783976A1 (en) | 2011-06-23 |
| JP2013514375A (ja) | 2013-04-25 |
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| IN2012DN05187A (enrdf_load_html_response) | 2015-10-23 |
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| US8569562B2 (en) | 2013-10-29 |
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| BR112012014736B1 (pt) | 2018-09-18 |
| WO2011075534A2 (en) | 2011-06-23 |
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